The invention relates to a process for the preparation of an N-substituted carbamoyl-lactam compound.
In the anionic polymerization of lactams, such as caprolactam, N-substituted carbamoyl-lactam compounds are suitable promoters, or activators, for the polymerization. These compounds can be used in the reaction-injection-molding (RIM) of nylon. Such compounds can provide short reaction times, which makes it possible to polymerize the lactam in the mold, without unduly long polymerization times.
Basically the reaction injection molding (RIM) method is a one-shot injection of liquid components, usually by impingement, into a closed mold where rapid polymerization occurs thereby resulting in a molded plastic product.
In a RIM process, viscosity of the materials fed to a mold is about 50 cps to 10,000 cps, preferably about 1500 cps, at injection temperatures varying from room temperature for urethanes to about 150.degree. C. for lactams. Mold temperatures in a RIM process typically range from about 100.degree. C. to about 220.degree. C. The mold pressures generally range from about 1 bar to 100 bar and more particularly, range from about 1 bar to about 30 bar. At least one component in th RIM formulation consists of monomers and adducts thereof that are polymerized to a polymer in the mold.
RIM differs from injection molding in a number of important respects. The main distinction between injection molding and RIM resides in the fact that in RIM, a chemical reaction takes place in the mold to transform a monomer or adducts to a polymeric state. Injection molding is conducted at pressures of about 700 bar to 1400 bar in the mold cavity by melting a solid resin and conveying it into a mold maintained at room temperature and the molten resin at about 150.degree. to 350.degree. C.
The pressures employed in the RIM method are much lower than in conventional injection molding processes. At injection temperature of about 150.degree. C. to 350.degree. C., viscosity of the molten resin in an injection molding process is generally in the range of 50,000 cps to 1,000,000 cps and typically about 200,000 cps. In injection molding process, solidification of the resins occurs in about 10 seconds to 90 seconds, depending on the size of the molded product, following which, the molded product is removed from the mold. There is no chemical reaction taking place in an injection molding process when the resin is introduced into a mold.
For practical purposes, in a RIM-process the chemical reaction must take place rapidly in less than about 2 minutes for smaller items.
The following developments in the anionic polymerization nylon are known.
The polymerization of a lactam to obtain nylon has been known for many years.
In U.S. Pat. No. 3,018,273 a process for the in situ polymerization of caprolactam is described, wherein an organomagnesium compound is used as an initiator, and an N,N diacyl compound is used as promoter (or activator).
British Pat. No. 1,067,153 describes a process for preparing nylon-block-copolymers by anionically polymerizing caprolactam in the presence of various activators suitable for preparing nylon 6 polymers. Preparation of nylon block copolymers using an isocyanate terminated polypropylene glycol and a potassium based catalyst is described; a nylon block copolymer containing at least one polyether block is thereby formed.
In U.S. Pat. Nos. 3,862,262, 4,031,164, 4,034,015 and 4,223,112 various aspects of the preparation of nylon block copolymers from caprolactam in the presence of an acyllactam activator are described.
U.S. Pat. Nos. 4,031,164 and 4,223,112 describe the lactam-polyol-polyacyl-lactam-block terpolymers having a specified ratio of the various components. More particularly, the former patent discloses the use of 18% to 90% by weight of polyol blocks in the terpolymer.
U.S. Pat. No. 3,862,262 describes lactam-polyol-acyl-polylactam block-terpolymers.
U.S. Pat. No. 4,034,015 is directed to lactam-polyol-polyacyl-lactam or lactam-polyol-acyl-polylactam block terpolymers having at least about 5% ester end group termination.
Reissue patent 30,371 describes preparing polyester-polyamide compounds by condensation of an alcohol and acyllactams in the presence of at least one of a Group IA, IIA, IIB, and IIIA metal or metal compound.
U.S. Pat. No. 3,925,325 describes a catalyzed process for the preparation of monomeric and/or polymeric compounds such as esters, polyesters, ester amides, and polyester-polyamides which result from the reaction of an imide and an alcohol in the presence of an organoaluminium, imide-alcohol condensation catalyst.
U.S. Pat. No. 3,965,075 describes using an amide or a Group IVA, IB, IVB, VB, VIB, or VIII organometal compound for this condensation.
In European patent application No. 67693, now laid open to public inspection, acid halide materials and acyllactam functional materials are described as useful in the preparation of nylon block copolymers selected from the group consisting of those having the formula: ##STR2## wherein A is X or Q,
X is halogen, PA1 Q is ##STR3## with PA1 (1) a polyester having a minimum molecular weight of 2,000, PA1 (2) a polyester containing polyester segments having minimum molecular weights of about 2000, PA1 (3) a segment of a hydrocarbon or PA1 (4) a polysiloxane. PA1 .sub.xi is an integer .gtoreq.2 PA1 R' is an alkyl, aralkyl, alkaryl or aryl group, whether or not cyclic, PA1 .sub.yi is an integer .gtoreq.0, PA1 (--L) is an unopened lactam ring and PA1 (--L--) is an opened lactam block. PA1 x.sub.i is an integer .gtoreq.2 PA1 R' is an alkyl, aralkyl, alkaryl or aryl group, whether or not cyclic, PA1 Y.sub.i is an integer .gtoreq.0, PA1 (--L) is an unopened lactam ring and PA1 (--L--) is an opened lactam block.
Y=C.sub.3 -C.sub.11 alkylene;
a is an integer equal to 1, 2 or 3; PA2 b is an integer equal to or greater than 2; PA2 R is a di- or polyvalent group selected from hydrocarbon groups and hydrocarbon groups containing ether linkages; and PA2 Z is a segment of:
European patent application No. 67,695, now laid open to public inspection, describes a process for preparing a nylon block copolymer by reactively contacting lactam monomer, basic lactam polymerization catalyst and the acyllactam functional material described in European patent application No. 67,693.
European patent application No. 67,694, now laid open for public inspection is directed to acid halide and acyllactam functional materials and to a process for the preparation of nylon block copolymers therewith. The acid halide or acyllactam functional materials are selected from the group defined by a complex formula.
Sibal et al, Designing Nylon 6 Polymerization Systems for RIM', apparently presented in part at the 2nd International Conference on Reactive Polymer Processing, Pittsburgh, Pa., in November 1982, described preparing various initiators for anionically polymerizing lactams including a polymeric initiator. This initiator is prepared by reacting hexamethylene diisocyanate (HDI) with a polypropylene oxide diol, having an average molecular weight of 2000, by slow addition of the polyol (1 mole) to two moles of HDI. The resulting product was reacted with anhydrous lactam at 80.degree. C. No mechanical properties data are reported on the final product. Indeed, further work is said to be required to begin exploring the processability and properties of the products. This paper also reports that reaction and other process governing parameters are not known and further work is required.
U.S. Pat. No. 4,400,490 describes the anionic polymerization of a lactam with an epoxy-compound in the presence of a basic catalyst and a promoter. The epoxy compound can be the reaction product of a polymeric polyol and an epoxy compound.
U.S. Pat. No. 3,793,399 describes the use of a polyol, soluble in molten caprolactam, for improving the impact resistance of polycaprolactam. An organic nitrogen compound is used as a promoter in the polymerization.
The use of etherified polyols in the anionic polymerization of caprolactam is described in U.S. Pat. No. 3,770,689.